JP2009514936A5 - - Google Patents
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- JP2009514936A5 JP2009514936A5 JP2008539493A JP2008539493A JP2009514936A5 JP 2009514936 A5 JP2009514936 A5 JP 2009514936A5 JP 2008539493 A JP2008539493 A JP 2008539493A JP 2008539493 A JP2008539493 A JP 2008539493A JP 2009514936 A5 JP2009514936 A5 JP 2009514936A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrrolo
- dihydro
- quinoline
- phenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 33
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- 241000893966 Trichophyton verrucosum Species 0.000 claims description 7
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- 206010013023 Diphtheria Diseases 0.000 claims description 6
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- 208000004396 Mastitis Diseases 0.000 claims description 6
- 208000005141 Otitis Diseases 0.000 claims description 6
- 208000000143 Urethritis Diseases 0.000 claims description 6
- 230000001580 bacterial Effects 0.000 claims description 6
- 201000000297 erysipelas Diseases 0.000 claims description 6
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- -1 1-methylbenzimidazol-2-yl Chemical group 0.000 claims 41
- 125000000217 alkyl group Chemical group 0.000 claims 35
- 125000005843 halogen group Chemical group 0.000 claims 31
- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000003545 alkoxy group Chemical group 0.000 claims 22
- 239000000203 mixture Substances 0.000 claims 20
- 244000005700 microbiome Species 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 9
- 230000000813 microbial Effects 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 6
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- 241000124008 Mammalia Species 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 239000002671 adjuvant Substances 0.000 claims 5
- 230000000240 adjuvant Effects 0.000 claims 5
- 239000003242 anti bacterial agent Substances 0.000 claims 5
- 239000000969 carrier Substances 0.000 claims 5
- 239000003085 diluting agent Substances 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 206010060945 Bacterial infection Diseases 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
- XCZMUTGHJBFKPM-UHFFFAOYSA-N 4-methyl-8-phenoxy-1-(2-phenylethyl)-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(CCC=4C=CC=CC=4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 XCZMUTGHJBFKPM-UHFFFAOYSA-N 0.000 claims 2
- OFEZSBMBBKLLBJ-BAJZRUMYSA-N CORDYCEPIN Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)C[C@H]1O OFEZSBMBBKLLBJ-BAJZRUMYSA-N 0.000 claims 2
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- IEDVJHCEMCRBQM-UHFFFAOYSA-N Trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
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- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
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- YKJYKKNCCRKFSL-RDBSUJKOSA-N (-)-anisomycin Chemical compound C1=CC(OC)=CC=C1C[C@@H]1[C@H](OC(C)=O)[C@@H](O)CN1 YKJYKKNCCRKFSL-RDBSUJKOSA-N 0.000 claims 1
- GAOZTHIDHYLHMS-GDMSFIFLSA-N (2R,3S,4R)-4-[(2R,5R,7S,8R,9S)-2-[(2R,5S)-5-ethyl-5-[(2S,3R,5S)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]oxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methylpentanoic acid Chemical compound C([C@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@@H]2[C@@H](C[C@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@H](C)[C@H](OC)[C@@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-GDMSFIFLSA-N 0.000 claims 1
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- FZNPGWDLTIHOCL-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinoline Chemical compound C1=C2C=3N(CC4OC5=CC=CC=C5OC4)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 FZNPGWDLTIHOCL-UHFFFAOYSA-N 0.000 claims 1
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- DDKUAZFTMXXZIS-UHFFFAOYSA-N 1-[3-(4-methyl-8-phenoxy-2,3-dihydropyrrolo[3,2-c]quinolin-1-yl)propyl]pyrrolidin-2-one Chemical compound C1=C2C=3N(CCCN4C(CCC4)=O)CCC=3C(C)=NC2=CC=C1OC1=CC=CC=C1 DDKUAZFTMXXZIS-UHFFFAOYSA-N 0.000 claims 1
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| US8940723B2 (en) | 2010-08-05 | 2015-01-27 | Helperby Therapeutics Limited | Combination of a pyrroloquinoline compound and a beta-lactam antimicrobial agent, mupirocin or chlorhexidine |
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| CA2811568A1 (en) | 2010-10-08 | 2012-04-12 | Helperby Therapeutics Limited | Novel composition |
| KR101254038B1 (ko) * | 2011-01-12 | 2013-04-12 | 한국화학연구원 | 퀴놀린올 화합물을 유효성분으로 포함하는 항진균 조성물 |
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| AU2013239696C1 (en) | 2012-03-27 | 2018-11-29 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| RU2015138796A (ru) | 2013-03-14 | 2017-04-19 | Семпра Фармасьютикалс, Инк. | Способы и составы для лечения респираторных заболеваний |
| BR112015023670A2 (pt) | 2013-03-15 | 2017-07-18 | Cempra Pharmaceuticals Inc | processo para preparar um composto |
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| WO2015192031A1 (en) * | 2014-06-12 | 2015-12-17 | Cem-102 Pharmaceuticals, Inc. | Compositions and methods for treating bone and joint infections |
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| CN108660189B (zh) * | 2018-05-30 | 2021-09-07 | 杭州千基生物科技有限公司 | 一种用于尿路感染病原体的量子点核酸检测的试剂盒 |
| CN109503569B (zh) * | 2019-01-03 | 2021-01-15 | 山东大学 | 噻唑类衍生物及其制备方法和应用 |
| US11896612B2 (en) | 2019-03-29 | 2024-02-13 | Board Of Trustees Of Michigan State University | Resurrection of antibiotics that MRSA resists by silver-doped bioactive glass-ceramic particles |
| CN111297852B (zh) * | 2019-12-05 | 2022-03-29 | 宁波大学 | 一种促进三疣梭子蟹雌蟹卵黄积累与卵巢发育的方法 |
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| GB202012797D0 (en) | 2020-08-17 | 2020-09-30 | Helperby Therapeautics Ltd | Disinfectant composition |
| WO2022047093A1 (en) | 2020-08-28 | 2022-03-03 | Incyte Corporation | Vinyl imidazole compounds as inhibitors of kras |
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| DE60227794D1 (de) * | 2001-04-26 | 2008-09-04 | Eisai R&D Man Co Ltd | Stickstoffhaltige verbindung mit kondensiertem ring und pyrazolylgruppe als substituent und medizinische zusammensetzung davon |
| IL165871A0 (en) | 2002-06-27 | 2006-01-15 | Schering Ag | Substituted quinoline CCR5 receptor antagonists |
| CL2004000409A1 (es) | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| US7875604B2 (en) | 2004-02-04 | 2011-01-25 | University Of Virginia Patent Foundation | Compounds that inhibit HIV particle formation |
| SI1740584T1 (sl) * | 2004-04-28 | 2009-06-30 | Takeda Pharmaceutical | Kondenziran kinolinski derivat in njegova uporaba |
| US20060074105A1 (en) | 2004-09-20 | 2006-04-06 | Serenex, Inc. | Substituted quinoline and quinazoline inhibitors of quinone reductase 2 |
| US20060183763A1 (en) | 2004-12-31 | 2006-08-17 | Pfizer Inc | Novel pyrrolidyl derivatives of heteroaromatic compounds |
| GB0522715D0 (en) * | 2005-11-08 | 2005-12-14 | Helperby Therapeutics Ltd | New use |
| US8940723B2 (en) * | 2010-08-05 | 2015-01-27 | Helperby Therapeutics Limited | Combination of a pyrroloquinoline compound and a beta-lactam antimicrobial agent, mupirocin or chlorhexidine |
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2005
- 2005-11-08 GB GBGB0522715.2A patent/GB0522715D0/en not_active Ceased
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2006
- 2006-11-08 PT PT68084722T patent/PT1945211E/pt unknown
- 2006-11-08 AU AU2006313590A patent/AU2006313590C1/en not_active Ceased
- 2006-11-08 BR BRPI0618374-3A patent/BRPI0618374A2/pt active Search and Examination
- 2006-11-08 EP EP06808472.2A patent/EP1945211B1/en active Active
- 2006-11-08 SI SI200632016T patent/SI1945211T1/sl unknown
- 2006-11-08 DK DK06808472.2T patent/DK1945211T3/en active
- 2006-11-08 CA CA2628729A patent/CA2628729C/en active Active
- 2006-11-08 NZ NZ568035A patent/NZ568035A/en not_active IP Right Cessation
- 2006-11-08 ES ES06808472.2T patent/ES2558685T3/es active Active
- 2006-11-08 RU RU2008122912/04A patent/RU2404982C2/ru not_active IP Right Cessation
- 2006-11-08 HU HUE06808472A patent/HUE026568T2/hu unknown
- 2006-11-08 CN CN2006800500487A patent/CN101351203B/zh active Active
- 2006-11-08 KR KR1020087013544A patent/KR101148049B1/ko active IP Right Grant
- 2006-11-08 JP JP2008539493A patent/JP5542336B2/ja active Active
- 2006-11-08 US US12/092,947 patent/US8207187B2/en active Active
- 2006-11-08 PL PL06808472T patent/PL1945211T3/pl unknown
- 2006-11-08 WO PCT/GB2006/004178 patent/WO2007054693A1/en active Application Filing
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2008
- 2008-05-05 IL IL191260A patent/IL191260A/en not_active IP Right Cessation
- 2008-05-22 ZA ZA200804454A patent/ZA200804454B/xx unknown
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2009
- 2009-07-20 HK HK09106583.1A patent/HK1127551A1/xx unknown
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2012
- 2012-05-17 US US13/473,707 patent/US9694006B2/en active Active
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2016
- 2016-01-13 HR HRP20160043TT patent/HRP20160043T1/hr unknown
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2017
- 2017-05-30 US US15/608,032 patent/US10493071B2/en active Active
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